As methods for producing a carbonyl compound by oxidizing alcohol, known are reactions using high valence chromium (Comprehensive Organic Synthesis; 1st ed.; B. M. Trost and I. Fleming, Ed.; Pergamon: Oxford, 1991; Vol. 7, pp. 251–289), manganese compounds (M. Hudlicky, Oxidations in Organic Chemistry; ACS Monograph Ser. 186; American Chemical Society: Washington, D.C., 1990), a high valence iodine compound (J Org. Chem., 1983, 48, 4155–4156), N-methylmorpholine N-oxide in the presence of a ruthenium catalyst (J. Chem. Soc. Chem. Commun., 1987, 1625–1627) and the like as the oxidizing agent. However, it is hard to say that these methods are industrially superior methods because of the large load on the environment in terms of the generation of by-products having high toxicity, corrosiveness of the oxidizing agents and the like.
On the other hand, it can be said that oxygen and hydrogen peroxide are excellent oxidizing agents in industrially applying them due to small environmental load, because they are inexpensive and have no corrosiveness, and there is no by-product after the reaction or it is harmless water.
As a method for producing a carbonyl compound from alcohol by using oxygen as the oxidizing agent, a method using a catalyst carrying a metal of Group 8 to 10 as the catalyst has been known (U.S. Pat. No. 4,218,401 specification), but this method requires a high temperature of 225 to 600° C.
On the other hand, as a method for producing a carbonyl compound from alcohol by using hydrogen peroxide as the oxidizing agent, a method using a catalyst carrying a metal of Group 8 to 10 as the catalyst has been reported (U.S. Pat. No. 6,232,505 specification), but the substrate is limited to water-soluble 1-methoxy-2-propanol which forms a homogenous phase with an aqueous hydrogen peroxide solution. In addition, the substrate must be used by preparing into a 20 wt % aqueous solution.
Also, an oxidation reaction of alcohol by using an aqueous hydrogen peroxide solution in which titanium silicate (TS-1) is used as the catalyst is known too (U.S. Pat. No. 4,480,135 specification), but in the oxidation reaction of water-insoluble alcohol, it is essential to use a polar organic solvent such as acetone for preparing a uniform solution by dissolving an oil solution of alcohol in an aqueous hydrogen peroxide solution. As a result, the reaction operation and apparatus become complex because of the necessity to employ a means for removing the polar organic solvent at the time of the isolation of a carbonyl compound as the product of interest. In addition, influence and toxicity of the polar organic solvent itself upon the environment and human body have been pointed out.